Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
  • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
  • C07D257/04—Five-membered rings
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
  • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
  • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof

Definitions

• the present invention relates to novel 1-(3-halo-4-substituted phenyl)tetrazolinone derivatives, to a process for their preparation, and to their use as herbicides.
• 1-(3-halo-4-substituted phenyl)tetrazolinone derivatives of the formula (I) are obtained when compounds of the formula (II) wherein X and Y have the above mentioned meanings, are reacted with compounds of the formula (III) wherein R1 and R2 have the above mentioned meanings, and R3 represents a releasable group such as chlorine or bromine atom, if appropriate, in the presence of acid binders, and in the presence of an inert solvent .
• novel 1-(3-halo-4-substituted phenyl)tetrazolinone derivatives of the formula (I) exhibit powerful herbicidal properties, particularly against paddy-field weeds.
• the 1-(3-halo-4-substituted phenyl)tetrazolinone derivatives according to the invention exhibit a substantially greater selective herbicidal action on paddy-field than the compounds known from the relevant prior art, (for instance, the aforementioned U.S Patents 4,956,469, 5,003,075 and 5,019,152 or EP-A-146,279 and EP-A-202,929).
• halogen includes fluorine, chlorine, bromine, and iodine, preferably chlorine or fluorine.
• the course of the reaction can be represented by the following equation:
• the starting compounds of the formula (II) mean compounds based on the above definitions of X and Y, preferably compounds based on the above preferred definitions.
• the compounds of the formula (II) can be obtained by the process disclosed, for example, in The Journal of Organic Chemistry, Vol. 45, No. 21, 1980, pages 5130 - 5136 or The Journal of American Chemical Society, Vol. 81, No. 7, 1980, pages 3076 - 3079.
• the starting compounds of the formula (III) mean compounds based on the above definition of R1 and R2, preferably compounds based on the above preferred definitions.
• the compounds of the formula (III) are well know in organic chemical field. As specific examples thereof, there may be mentioned: Diisopropylcarbamoyl chloride or bromide, Diethylcarbamoyl chloride or bromide, Diallylcarbamoyl chloride or bromide, and Dipropylcarbamoyl chloride or bromide.
• diluents examples include water; aliphatic, cycloaliphatic and aromatic, optionally chlorinated, hydrocarbons such as pentane, hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, dichlorobenzene and the like; ethers such as diethyl ether, methyl ethyl ether, di-isopropyl ether, dibutyl ether, dioxane, dimethoxyethane (DME), tetrahydrofurane (THF), diethyleneglycol dimethylether (DGM), and the like; nitriles such as acetonenitrile, propionitrile and the like; acid amides such as dimethyl formamide (DMF), dimethyl acetamide (DM
• the process according to the invention is carried out preferably in the presence of acid binder and as example of such acid binder may be mentioned inorganic bases including hydroxide, carbonate, bicarbonate, alcolate of alkali metals and alkali metal hydride such as, for example, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide and the like; inorganic amides of alkali metals such as lithium amide, sodium amide, potassium amide and the like, and organic bases including tertiary amines, dialkylaminoanilines, and pyridines such as, for example, triethylamine, tributyl-amine, 1,1,4,4-tetramethylene-diamine (TMEDA), N,N-dimethylaniline, N,N-diethylaniline, pyridine, 4-dimethylamino pyridine (DMAP), 1,4-diazabicyclo-[
• organic lithium compounds such as methyl lithium, n-butyl lithium, sec-butyl lithium, tert-butyl lithium, phenyl lithium, dimethyl copper lithium, lithium diisopropyl amide, lithium cyclohexylisopropyl amide, lithium dicyclohexyl amide, n-butyl lithium ⁇ DABCO, n-butyl lithium ⁇ DBU, n-butyl lithium ⁇ TMEDA and the like.
• the reaction temperature can be varied within a substantially wide range.
• the reaction is carried out at a temperature of from about -80°C to about 200°C, preferably from about -10°C to about 130°C.
• reaction is carried out under normal pressure, although it is also possible to employ a higher or reduced pressure.
• the desired compounds of the formula (I) can be obtained by reacting of about 1.0 to 1.3 mol of the compounds of the formula (III) per 1 mol of the compounds of the formula (II), in a diluent such as acetonitrile, in the presence of 1 to 1.3 mol of acid binder.
• the active compounds according to the invention can be used as defoliants, desiccants, agents for destroying broad-leaved plants and, especially, as weed killers.
• weeds in the broadest sense, there are to be understood all plants which grow in locations where they are undesired. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
• the active compounds according to the invention can be used, for example, in connection with the following plants: Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver and Centaurea.
• the compounds are suitable, depending on the concentration, for the total combating of weeds, for example on industrial terrain and rail tracks, and on paths and squares with or without tree plantings. Equally, the compounds can be employed for combating weeds in perennial cultures, for example afforestation, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea Plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hop-fields, and for the selective combating of weeds in annual cultures.
• the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, foams, pastes, granules, aerosols, natural and synthetic materials impregnated with active compound, very fine capsules in polymeric substances, coating compositions for use on seed, and formulations used with burning equipment, such as fumigating cartridges, fumigating cans and fumigating coils, as well as ULV cold mist and warm mist formulations.
• customary formulations such as solutions, emulsions, wettable powders, suspensions, powders, foams, pastes, granules, aerosols, natural and synthetic materials impregnated with active compound, very fine capsules in polymeric substances, coating compositions for use on seed, and formulations used with burning equipment, such as fumigating cartridges, fumigating cans and fumigating coils, as well as ULV cold mist and warm mist formulations.
• formulations may be produced in known manner, for example by mixing the active compounds with extenders, that is to say liquid or liquefied gaseous or solid diluents or carriers, optionally with the use of surface-active agents, that is to say emulsifying agents and/or dispersing agents and/or foam-forming agents.
• extenders that is to say liquid or liquefied gaseous or solid diluents or carriers
• surface-active agents that is to say emulsifying agents and/or dispersing agents and/or foam-forming agents.
• organic solvents can, for example, also be used as auxiliary solvents.
• liquid solvents diluents or carriers there are suitable in the main, aromatic hydrocarbons, such as xylene, toluene or alkyl napthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, or strongly polar solvents, such as dimethylformamide and dimethyl-sulphoxide, as well as water.
• aromatic hydrocarbons such as xylene, toluene or alkyl napthalenes
• chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloro
• liquefied gaseous diluents or carriers liquids which would be gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
• ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth
• ground synthetic minerals such as highly-dispersed silicic acid, alumina and silicates.
• crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks.
• non-ionic and anionic emulsifiers such as polyoxyethylene-fatty acid esters, polyoxyethylene-fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulphonates, alkyl sulphates, aryl sulphonates as well as albumin hydrolysis products.
• Dispersing agents include, for example, lignin sulphite waste liquors and methylcellulose.
• Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, can be used in the formulation.
• colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs or metal phthalocyanine dyestuffs, and trace nutrients, such as salts of iron, manganese boron, copper, cobalt, molybdenum and zinc.
• organic dyestuffs such as alizarin dyestuffs, azo dyestuffs or metal phthalocyanine dyestuffs
• trace nutrients such as salts of iron, manganese boron, copper, cobalt, molybdenum and zinc.
• the formulations in general contain from 0.1 to 95 per cent by weight of active compound, preferably from 0.5 to 90 per cent by weight.
• the active compounds according to the invention can also be used, for combating weeds, as mixtures with known herbicides, finished formulations or tank mixes being possible.
• the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing or scattering.
• the active compounds according to the invention can be applied either before or after emergence of the plants.
• the amount of active compound used can vary within a substantial range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 0.01 and 10 kg of active compound per hectare of soil surface, preferably between 0.01 and 2 kg per ha.
• Each of several pots having a size of 25 x 20 x 9 cm and an area of 1/2,000 are, was filled with soil taken out from a paddy field.
• Table 1 Active compound No. Dosage of active compound (g/ha) Herbicidal effect (%) Phytotoxicity (%) A B C D E rice 1 500 100 100 100 100 100 10 250 90 100 98 98 98 10 2 500 100 100 100 100 100 10 250 90 100 70 100 100 0 3 500 100 100 98 100 100 100 0 250 90 100 95 70 100 0 c C 500 0 0 0 0 0 0 wherein A represents barnyard grass; B represents flatsedge; C represents monochoria; D represents broad-leaved weeds; and E represents Scirpus juncoides Roxb var. Hotarui Ohwi.

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• Organic Chemistry (AREA)
• Chemical & Material Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Dentistry (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Plant Pathology (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Pest Control & Pesticides (AREA)
• Agronomy & Crop Science (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Plural Heterocyclic Compounds (AREA)

Applications Claiming Priority (2)

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Cited By (9)

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• 1992
  • 1992-06-03 JP JP04166772A patent/JP3102954B2/ja not_active Expired - Fee Related
• 1993
  • 1993-05-07 AU AU38452/93A patent/AU656671B2/en not_active Ceased
  • 1993-05-17 EP EP93107994A patent/EP0572855A1/fr not_active Withdrawn
  • 1993-05-21 KR KR1019930008804A patent/KR940000439A/ko not_active Application Discontinuation
  • 1993-05-26 US US08/067,374 patent/US5342954A/en not_active Expired - Fee Related
  • 1993-05-27 HU HU9301555A patent/HUT65424A/hu unknown

Patent Citations (2)

Non-Patent Citations (2)

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